2-alkoxy-2-oxazolines



United States Patent "ice l, 1 3 ,12

ines are produced from the indicated aziridines as shown 3,198,396 in the following table. Z-ALKOXY-Z-OXAZOLINES George E. Ham, Lake Jackson, Tex, assignor to The Dow Chemical Company, Midland, Mich, a corporation of 0 C Delaware 5 R0 4; R0 No Drawing. Filed Aug. 7, 1963, Ser. No. 300,643 T T 3 Ciaims. (Ci. 260-307) 7 CH2 0-CH,

This invention relates to new compounds having the N formula 10 Aziridine Oxazoline R R! RI! N-C RR" R0C n-Propyl H H 2-Propoxy-2-oxazoline.

\ n-Butyl H CH3 2-But0xy-4-rnethyl-2- O OH2 oxazohne.

Benzyl- F1 W 2-Benzyloxy-2-oxazolme. Cyclohexyl H H 2-Cyclohexyloxy-2- oxazoline. sec.-Amyl H H 2-sec.-Amy1oxy-2- oxazoline. wherein R is an alkyl, aralkyl or cycloalkyl radical and 0 Y H H Y R and R" are H, alkyl, cycloalkyl or phenyl radicals. Ethyl z-Eltlhoxggmethlyli- The compounds of the invention are conveniently pre- P 3 Oxazo i110- -'h 4- 1 tl-4- pared by the molecular rearrangement of the correspond- Ethyl Cyclopentyl Bum 2 y inc aziridine; Ethyl AmyL. Amyl.-. 2-Etl1oxy-4,4-diamyl-2- b Oxazoline.

0 CRIB, I a I a O H The oxazolines listed above are clear liquids having R C properties and uses similar to those of 2-ethoxy-2-oxazol- CH: ine. For practical reasons of availablity of materials we prefer the compounds having the above formulas wherein R is a lower alkyl group, i.e., R contains 1 to 8 carbon I atoms, and R' and R are hydrogen or lower alkyl. Also, Tlflls fearl'angFment efiected y Warm-111g the azlndme it is preferred that any cycloalkyl radicals contain 5 or 6 with an a1l al1 metal lodide. The reaction is preferably carbon atomsin the cydoalkyl i conducted an a suitable solvent at a temperature of about The i idi lf r at used as Starting matenals are P Sultable solvents mfflude acetomtlfle, P conveniently prepared by the reaction of the appropriate piomtrlle, dime'thyl formamide, dimethyl sulfoxide and aziridine with the appropriate hl r f r at ethylene carbonate.

A convenient general procedure for making the new 40 compounds by rearrangement of the appropriate aziridine 0 consists essentially of dissolving the aziridine in a suit- ROCQC1+ HN g able solvent, such as acetonitrile, adding about 520% by weight of alkali metal iodide, heating for at least several hours at about 60100 C. and separating the product from the reaction mixture. This procedure is A tertiary amine or other acid acceptor should be used. illustrated by the following example. The 2-alkoxy-2-oxazolines can be made less conven- A mixture of 23 g. of ethyl l-aziridinylformate, 3 g. of iently by other methods, as, for instance, by the ring clo- NaI and 300 m1. of acetonitrile Was refluxed (at about 80 sure by caustic of the appropriate haloalkyl carbamate. C.) for four days. It was then cooled to l0 C. and filtered. The solvent was removed from the filtrate by distillation under reduced pressure, after which the prodnot was distilled at 40 C./1 mm. Upon redistillation :4 RR R a H it yielded 10.7 g. (47% conversion) of 2-ethoxy-2-oxazo- 0H,o

line, a colorless liquid having the fo1lowin properties: N 01 H 0 B.P., 96 C./lO0mm.;n 2o, ;P H a a 53.31; percent H, 7.85 (calcd, c, 52.16; H, 7.88 R R When dry HCl was passed into an ether solution of the 1. A compound having the formula carbamate.

Z-ethoxy-Z-oxazoline was found to be an effective sta- GER bilizer for trichloroethylene when incorporated therein in an amount of about 0.02% by volume.

By use of the above general procedure, other 2-oxazolwherein R is a radical selected from the group consisting of alkyl, hydrocarbon aralkyl and cycloalkyl radicals and R and R" are radicals selected from the group consisting of H, alkyl, cycloalkyl and phenyl radicals and wherein each of the radicals R, R and R" contains not more than 8 carbon atoms :and each cycloalkyl radical contains 5 to 6 carbon atoms in the cycloalkyl ring.

2. A compound having the formula N-GH; R 0 0 wherein R is a lower alkyl radical.

3. 2-ethoxy-2-oxazoline.

References Cited by the Examiner Beilsteins Handbuch der Organischen Chcrnie, vol. 27 (Berlin, 1937), page 94.

Chem. Abstracts, vol. 51, page 1696s (subject Index, J-Z) (1957).

Conant et al.: The Chemistw of Organic Compounds (New York, 1947), pages 342-345.

Lowy et 211.: Introduction to Organic Chemistry (New York, 1945), pages 213-215.

Solotorovsky et al.: Chem. Abstracts, vol. 51, page 3821d (1957).

NICHOLAS S. RIZZO, Primary Examiner.

WALTER A. MODANCE, Examiner. 

1. A COMPOUND HAVING THE FORMULA 